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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2020-02-26 21:41:29 UTC
HMDB IDHMDB0015376
Secondary Accession Numbers
  • HMDB15376
Metabolite Identification
Common NameTrimeprazine
DescriptionTrimeprazine, also known as repeltin or methylpromazine, belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring. It also acts as a sedative, hypnotic, and antiemetic for prevention of motion sickness. Although it is structurally related to drugs such as chlorpromazine, it is not used as an antipsychotic. In the Russian Federation, it is marketed under the brand name Teraligen for the treatment of anxiety disorders (including GAD), organic mood disorders, sleep disturbances, personality disorders accompanied by asthenia and depression, somatoform autonomic dysfunction and various neuroses. Alimemazine is not approved for use in humans in the United States. Trimeprazine is a drug. Trimeprazine is a very strong basic compound (based on its pKa). In humans, trimeprazine is involved in oxomemazine h1-antihistamine action. The combination of alimemazine and prednisolone (commonly sold under the brand name Temaril-P) is licensed as an antipruritic and antitussive in dogs.
Structure
Data?1582753289
Synonyms
ValueSource
RepeltinKegg
MethylpromazineKegg
AlimemazineKegg
TrimeperazineHMDB
NedeltranHMDB
Evans brand OF alimemazine tartrateHMDB
PanectylHMDB
Pierre fabre brand OF alimemazineHMDB
Rhône poulenc rorer brand OF alimemazine tartrateHMDB
Rhône-poulenc rorer brand OF alimemazine tartrateHMDB
SpansuleHMDB
ThéralèneHMDB
IsobutrazineHMDB
VariargilHMDB
Alimemazine italfarmaco brandHMDB
Allergan brand OF alimemazine tartrateHMDB
Italfarmaco brand OF alimemazineHMDB
VallerganHMDB
TrimeprazineKEGG
Chemical FormulaC18H22N2S
Average Molecular Weight298.446
Monoisotopic Molecular Weight298.150369404
IUPAC Namedimethyl[2-methyl-3-(10H-phenothiazin-10-yl)propyl]amine
Traditional Nametrimeprazine
CAS Registry Number84-96-8
SMILES
CC(CN(C)C)CN1C2=CC=CC=C2SC2=CC=CC=C12
InChI Identifier
InChI=1S/C18H22N2S/c1-14(12-19(2)3)13-20-15-8-4-6-10-17(15)21-18-11-7-5-9-16(18)20/h4-11,14H,12-13H2,1-3H3
InChI KeyZZHLYYDVIOPZBE-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenothiazines. These are polycyclic aromatic compounds containing a phenothiazine moiety, which is a linear tricyclic system that consists of a two benzene rings joined by a para-thiazine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazines
Sub ClassPhenothiazines
Direct ParentPhenothiazines
Alternative Parents
Substituents
  • Phenothiazine
  • Alkyldiarylamine
  • Diarylthioether
  • Aryl thioether
  • Tertiary aliphatic/aromatic amine
  • Para-thiazine
  • Benzenoid
  • Tertiary amine
  • Tertiary aliphatic amine
  • Thioether
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point68 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0084 g/LNot Available
LogP4.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0084 g/LALOGPS
logP4.82ALOGPS
logP4.41ChemAxon
logS-4.6ALOGPS
pKa (Strongest Basic)9.42ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area6.48 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity93.37 m³·mol⁻¹ChemAxon
Polarizability34.83 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9010000000-3652afb69d877d9e3ef5Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9240000000-3d6ddecfeef1ce4ea2a2Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0002-1192000000-93fd466d9dd2ccc3c679Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9010000000-3652afb69d877d9e3ef5Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-9240000000-3d6ddecfeef1ce4ea2a2Spectrum
GC-MSGC-MS Spectrum - CI-B (Non-derivatized)splash10-0002-1192000000-93fd466d9dd2ccc3c679Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-08fr-7190000000-0f8a5eefc8992f88c42eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0f6t-0390000000-d19c7e0d929f71a4ad36Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-3790000000-934bfb5b005b12a5e73dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pc3-9310000000-63ebd221a8008ee5907eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0190000000-2baf4399efd26ce01a1aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000b-0950000000-4297ad548b801681761cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-2900000000-a79d6af3311c241ede5fSpectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01246 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01246 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01246
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5373
KEGG Compound IDC07172
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAlimemazine
METLIN IDNot Available
PubChem Compound5574
PDB IDNot Available
ChEBI ID157833
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular weight:
55783.6
References
  1. Santos DE, Liu GJ, Takeuchi H: Blockers for excitatory effects of achatin-I, a tetrapeptide having a D-phenylalanine residue, on a snail neurone. Eur J Pharmacol. 1995 Jan 16;272(2-3):231-9. [PubMed:7713167 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]